My first experience with a guy

[Oshkosh60]

I think it is a sign that your wife suspects you are up to something..... so..... is getting fucked in the ass by a guy in a hotel worth getting fucked in the ass by your wife in divorce court ? Hmmmm ? Maybe ?

 

[MrMannson]

I think it is a sign that your wife suspects you are up to something..... so..... is getting fucked in the ass by a guy in a hotel worth getting fucked in the ass by your wife in divorce court ? Hmmmm ? Maybe ?

Haha you hit the nail on the head! Well said!

 

[Scooter58]

Haha you hit the nail on the head! Well said!

I wish lit had an icon that you could post so that when you opened it up to read it, the “sad trombone “ sound effect would play audibly. That is often the most appropriate response to all of us who have had “boner killing” moments.

 

[MrMannson]

I wish lit had an icon that you could post so that when you opened it up to read it, the “sad trombone “ sound effect would play audibly. That is often the most appropriate response to all of us who have had “boner killing” moments.

Tell me about it. I can’t stop thinking about the missed opportunity. I go from angry to sad! I guess it’s back to video chat and Lit for now

 

[Scooter58]

I dare say just about every single guy posting on Lit threads has felt that moment of despair and disappointment. Maybe some gals too. I’ve had plenty of disappointments that were out of my control and several missed opportunities that I didn’t capitalize on and those really hurt because when I think about them, all I can think about is Homer Simpson…”Doh!”

 

[KeenVoyeur]

We have some VERY friendly neighbours . I’ll message you with details about our experiences. If anyone else reads this and wants to chat about my pegging experiences, message me in Forums and I’m happy to share!

DMs are open ... love to hear more about your experiences! Guess I'm living in the wrong neighbourhood - but an invite to one of your parties might be nice

 

[budlight69]

Is it a sign, or ???
I was creeping so close to my first bisexual experience. I was talking back and forth with some guys on Sniffies, and on here.
Went out of town for work last week. Was hoping to pop my bi cherry with a mutual jerk off or something while at the hotel room. I was hard and so excited.
Last minute, my wife invited herself along. Fuck. Anyhow, Thursday night I was out of my shower, and logged onto Sniffies. For hells sake, another user was in the same hotel!! He saw I was there based on my location and invited me to the hot tub! My heart was beating; how could I get away from my wife and have my first blowjob? Fuck!

Anyhow, I had to disappear because she was keeping an eye on me like a hawk. I don’t know when the next opportunity will come up like that, if ever, but I feel like my chance is gone and I’m left to wonder what if….

Hard to get away for me too. I was recently about to finally meet a buddy I met on Lit but of course something came up (death in wife's family) when the time came. Hoping for another opportunity soon.

 

[Dreamer110]

Hard to get away for me too. I was recently about to finally meet a buddy I met on Lit but of course something came up (death in wife's family) when the time came. Hoping for another opportunity soon.

So close. Must be frustrating.

 

[TallOne]

I wish lit had an icon that you could post so that when you opened it up to read it, the “sad trombone “ sound effect would play audibly. That is often the most appropriate response to all of us who have had “boner killing” moments.

My wife and I swing and have had plenty of bi experiences with that. But my sad trombone story was from this past weekend. She had a fwb over and I had permission to have a guy over for solo play for the first time. He's been over before to play with both of us and he has fucked me. He's excited about it all week as am I.

Then 20 mins before he's supposed to head over he just stops responding to texts and ghosts me. I try a couple alternates but no one is available. Nothing like having the perfect and fully approved by the wife opportunity just to get ghosted.

 

[Biguy77578]

Walked in on my best friend of 30
Years taking a piss.. I jokingly said nice cock.. I’ve seen it a bunch of times over the years in locker rooms showers ect. It was his girlfriend’s 30th b day party . I whip mine out and started pissing next to him and said it’s only skin on a stick. We started
Laughing and went about our night. After everyone left the party it was the three of us and his girlfriend mentioned she heard we shared the bathroom. Then she starts telling us how hot that was and that it really made her wet the thought of two guys going at it.
She asked if we would suck each others cocks. Before I could say anything my buddy had my cock out and was blowing me. She immediately got naked and we spent the next three hours sucking and fucking. I came multiple times but he was still going strong. While I tried to get hard again I watched her fuck him with a dildo then we flipped him over and her and I blew him together until he came all over both of our faces . It was the hottest night of my life .

Very very very hot! Amazing you have over 50 LIKES!

 

[anotherfred]

I had a good friend and would frequently spend the night at his house. He broached the subject of sex by talking about his masturbation habits and encouraging me to share mine. I think he was the first one to whom I admitted doing it. He had a queen bed that we both slept in when I stayed there and we'd end up horny late at night. One night he said that he was so horny he wanted to try something new, and asked if I'd be up for something too. We made out and stroked each other's cocks. It was fascinating because his cock was skinnier and stiffer than mine and felt very different to jack off. I came pretty quickly and had a little post-orgasm freak out because we lived in a fairly conservative and homophobic community. I didn't get him off, which I regret to this day. I like to think about waking him up the next morning with my hand down his pants.

Anyway, my freak out caused us to grow apart, but I realized that I liked what we did. I was very into girls, but I had some private crushes on other boys that I never acted on. Wish I had, because one of them came out gay during college and we probably could have had some fun together.

A couple years later, my earlier friend was having a party and several friends and I were sleeping over. We weren't as close as we had been, but we had a lot of mutual friends. While most of the guys were setting up their sleeping bags downstairs, he asked if I wanted to come sleep in his bed again. That got my mind racing! I had thought a lot about our earlier experiences and had hoped for another opportunity to come up. By this time, i was mentally prepared to get him off and go at least a little further.

I forget how the subject came up, but finally I asked if he might be horny to try something again. Of course he said yes, and I went down and sucked his cock until he came in my mouth. He stroked me to an orgasm.

Sadly, we didn't hook up again, but about a year after that a mutual friend asked me to sleep over. Looking back, I suspect that our friend had pointed him in my direction. At that sleepover he started talking about sex, and he brought up the Hite report, and in particular the responses about male-male experimentation and fun.

We sucked each other off that night, but it only happened that once

 

[dobbins1]

Bump it?

 

[Vaslim74]

My first experience was when I was in my early 40’s. That is when I became more open minded about things. I was meeting up with a couple in their early 60’s. The husband was bi and wanted to suck my cock and I was going to let him, but there was no pressure for me to return the favor. When I got to their hotel room, they gave me a drink to relax. The wife and I finally started making out, next thing I know her husband had my pants down around my ankles and was sucking my cock! Before I realized it where on the bed in a circle of sorts, I was eating her, she was sucking him and he was sucking me. Next thing I know I was sucking his cock and his wife was sucking mine. When I started fucking his wife he was watching, at some point I bend her over fucking her doggy and he stood up next to me and I sucked his cock while fucking her! Doing that made me cum so hard. During the rest of that night I sucked him and he would suck me hard for his wife. It was a great night, I surprise myself for sure. But I did enjoy sucking his cock. Now older I still crave sucking a nice cock.

 

[Uncut1969]

My first experience was when I was in my early 40’s. That is when I became more open minded about things. I was meeting up with a couple in their early 60’s. The husband was bi and wanted to suck my cock and I was going to let him, but there was no pressure for me to return the favor. When I got to their hotel room, they gave me a drink to relax. The wife and I finally started making out, next thing I know her husband had my pants down around my ankles and was sucking my cock! Before I realized it where on the bed in a circle of sorts, I was eating her, she was sucking him and he was sucking me. Next thing I know I was sucking his cock and his wife was sucking mine. When I started fucking his wife he was watching, at some point I bend her over fucking her doggy and he stood up next to me and I sucked his cock while fucking her! Doing that made me cum so hard. During the rest of that night I sucked him and he would suck me hard for his wife. It was a great night, I surprise myself for sure. But I did enjoy sucking his cock. Now older I still crave sucking a nice cock.

Wow sounds like a great relationship you had with them ! I wish I could have a relationship like that!

 

[bromorob79]

My first time was in my mid 30s on a fishing trip with my best friend. I'm happily married and had never thought of doing anything with a man before that. Started as flashing each other for a laugh and just kind of naturally progressed from there. Still hard to believe it happened.

Tbh the whole reason I joined this site was to write about it, because I've never told anyone in real life and wanted to get it off my chest.

If anyone is interested, this is the first of 4 parts:

https://www.literotica.com/s/greg-with-benefits-1

 

[Biguy77578]

My first time was in my mid 30s on a fishing trip with my best friend. I'm happily married and had never thought of doing anything with a man before that. Started as flashing each other for a laugh and just kind of naturally progressed from there. Still hard to believe it happened.

Tbh the whole reason I joined this site was to write about it, because I've never told anyone in real life and wanted to get it off my chest.

If anyone is interested, this is the first of 4 parts:

https://www.literotica.com/s/greg-with-benefits-1

My best friend from high school and I had a sexual relationship also. After school and college both of us married found the best way to have alone time was fishing trips. I had a fishing camp in Galveston Bay and the only way to get to it was by boat so privacy was assured. We would go out on Friday afternoons and fish, suck and fuck until Sunday. Great memories!

 

[TerriC]

My first was a complete miss. I was 18 and went to a local ABS. I was in a viewing booth and the first channel that came up was two dudes. I was kind of into it when I noticed a finger coming through a hole in the wall. It scared the hell out of me, I ran out of that store as fast as I could.
My first real experience came much later. I had been chatting with a guy on a dating site, we finally got to meet and he showed me the joys of sucking

 

[Uncut1969]

I am so ready for my first experience! A couple of no shows was a big disappointment! Would love a fwb to be a regular and open up a new enjoyment instead of my hand !

 

[SaraSera]

My first time with a guy was at 19 and arranged for me by an older woman who was my only other sexual partner. The event was an in home prom as I had never been to one. She made dinner and in general chaperoned the night providing prompts to initiate conversations and actions on my part as I was clueless in regards to everything related dating and social interaction. (Repressed androgynous teen with friends but no relationship experience). I made it through dinner and dancing was suggested. He felt fantastic as I melted into his embrace while an intense feeling of dizzying giddiness bloomed inside me. Looking over his shoulder I saw Beth (my enabling friend, teacher and confidant) frantically mouthing “kiss him”. Best advice ever! Small kisses on his neck started events moving quickly. His hands became active caressing my body and cupping my ass lifting slightly. Neck kisses turned into deep slow kisses leaving me moaning. My hands had their own agenda as I don’t recall thinking about groping him but I did find my hands full of a hardening flesh and blood cock that wasn’t my own. There is obviously a segue between that point and where I was face to face with my first dick but I can’t say what it was. I do remember an uncut beautiful cock with a glistening head and feeling it pass between my lips and onto my tongue. Soft, pliant and yielding while hard at the same time. I want to say I was a natural but all I was able to do was try to imitate what Beth had done to me that I liked. I kept his head in my mouth and used my tongue decidedly un artfully and alternating sucking and humming. I was probably the worst blow job of his life to that point. (He was 24) We moved into the bedroom where he removed my dress kissing each area as it became uncovered leaving me in panties and thigh high stockings. His foreplay was experienced and deft and he kept me breathless. Eventually his fondling found the small plug Beth pointedly suggested I wear and he gripped it and gave a small tug before asking permission. So properly lubed and pre-stretched I was mounted astride him with my virgin to real cock ass about cancel that status. The first thing I noted was the soft feeling of his glans as opposed to the strap on I was used to. The second thing was the heat of real flesh as opposed to the strap on. The third thing I noticed came after positions were changed and he orgasmed into me. I felt every pulse of his orgasm and later the result dripping out of me. Much later that night Beth coached me though a less traumatic experience for him where I had my first bj to completion which I think was more rewarding for me than him . So that’s my first time with a guy.

 

[liqueur]

My first time with a guy was at 19 and arranged for me by an older woman who was my only other sexual partner.

Wonderful story. And so great to have a mentor like that.

 

[SaraSera]

Wonderful story. And so great to have a mentor like that.

It was. She was a hands on sex ed instructor who engaged in lab work extensively.

 

[stargame]

My first time with a guy was at 19 and arranged for me by an older woman who was my only other sexual partner. The event was an in home prom as I had never been to one. She made dinner and in general chaperoned the night providing prompts to initiate conversations and actions on my part as I was clueless in regards to everything related dating and social interaction. (Repressed androgynous teen with friends but no relationship experience). I made it through dinner and dancing was suggested. He felt fantastic as I melted into his embrace while an intense feeling of dizzying giddiness bloomed inside me. Looking over his shoulder I saw Beth (my enabling friend, teacher and confidant) frantically mouthing “kiss him”. Best advice ever! Small kisses on his neck started events moving quickly. His hands became active caressing my body and cupping my ass lifting slightly. Neck kisses turned into deep slow kisses leaving me moaning. My hands had their own agenda as I don’t recall thinking about groping him but I did find my hands full of a hardening flesh and blood cock that wasn’t my own. There is obviously a segue between that point and where I was face to face with my first dick but I can’t say what it was. I do remember an uncut beautiful cock with a glistening head and feeling it pass between my lips and onto my tongue. Soft, pliant and yielding while hard at the same time. I want to say I was a natural but all I was able to do was try to imitate what Beth had done to me that I liked. I kept his head in my mouth and used my tongue decidedly un artfully and alternating sucking and humming. I was probably the worst blow job of his life to that point. (He was 24) We moved into the bedroom where he removed my dress kissing each area as it became uncovered leaving me in panties and thigh high stockings. His foreplay was experienced and deft and he kept me breathless. Eventually his fondling found the small plug Beth pointedly suggested I wear and he gripped it and gave a small tug before asking permission. So properly lubed and pre-stretched I was mounted astride him with my virgin to real cock ass about cancel that status. The first thing I noted was the soft feeling of his glans as opposed to the strap on I was used to. The second thing was the heat of real flesh as opposed to the strap on. The third thing I noticed came after positions were changed and he orgasmed into me. I felt every pulse of his orgasm and later the result dripping out of me. Much later that night Beth coached me though a less traumatic experience for him where I had my first bj to completion which I think was more rewarding for me than him . So that’s my first time with a guy.

What a beautiful experience. I love it where you said you melted into his arms.

 

[MrFox702]

My first gay experience was with guy I knew from school, he was very open about sex and admitted to me he found men more of a turn on, I asked him if he had ever had an experience with another male, he said no but fantasised a lot and masturbated many times thinking of sexual scenarios with men, I said I also masturbated quite often about the same subject.
We lived on a council estate and gay sex was taboo around that time fortunately at the back of where I lived were open fields full of thigh length crops, I arranged to meet with this man I was eager to hear more from him and his thoughts, so we walked through the fields until we were out of sight and I said do you mind if we sat down for a while, and I started to ask him more if he would like to have a gay experience if given the chance, I asked him if he would like to masturbate me because I was turned on with his sexual chat, he told me let me see your cock so I untied my shorts and got them down to my knees, he could see I was fully erect from the bulge in my pants and he slid his hand inside and held my balls and massaged them gently then he put his hand on the waistband of my pants and pulled them over my cock exposing my full erection, he then put his hand around my cock and started to wank me I could hear the sound of the precum that had leaked from my cock with each stroke, he continued to massage my balls and wank me with the other hand I could feel the build up of spunk that was going to explode I told him don’t stop this is an amazing feeling, I’m gonna cum I said and I could feel his warm breath close to my hard cock and then his tongue licking the underside of my cock I couldn’t hold it any longer and spunk erupted from me all over my mates mouth and face, he masturbated over my face his knees either side of my shoulder and his cock directly above my mouth and he exploded his spunk all over my face in my hair up my nose and in my mouth, we repeated our meets always ending up with masturbation and oral, I’m still awaiting to be penetrated though, my friend moved away sadly and I often wonder what he’s doing now.

 

[SaraSera]

What a beautiful experience. I love it where you said you melted into his arms.

Beth chose well. I still feel bad about the horrid bj I attempted. I should have looked him up once I got better to make it up to him.

 

[stargame]

Beth chose well. I still feel bad about the horrid bj I attempted. I should have looked him up once I got better to make it up to him.

The second time around is bound to be better for both of you.